90s Shoes That Will Never Go Out Of Style

There is a certain stereotype about women and shoes — namely, that we love them a little too much. That no matter how many pairs we have, it never seems to be enough. As Carrie Bradshaw, one of TV's most infamous shoe lovers, once said, "I've spent $40,000 on shoes and I have no place to live? I will literally be the old woman who lived in her shoes!" 

Whether you're a shoe obsessive or not, there's always something exciting about a new pair — especially a pair that never goes out of style. While shoe trends come and go, there are some that always seem to be filling the shelves and the streets. In honor of the '90s fashion renaissance, we've decided to take a look back at some of the most popular shoe styles of the decade. So, without further ado, here are the '90s shoe styles that will never go out of style.

The chunky Mary Jane

Mary Janes sometimes get a bad rap for looking a little too similar to school shoes. The classic design features a rounded shape and a single buckle with a strap. While you may think of preppy schoolgirls when you think of Mary Janes, it turns out not all Mary Janes are alike. In fact, a certain style of Mary Janes that came out of the '90s are still going strong today: the chunky Mary Janes.

Unlike the iconic schoolgirl Mary Janes, the '90s version features a chunky platform giving the shoe a grownup edge. "The effortless chic of the Mary Jane style is the reason why our clients are drawn to this silhouette year after year," Cassie Smart, head of womenswear at MatchesFashion, told Harper's Bazaar in 2022. Added Marina Larroudé, founder of Larroudé, "Mary Janes have that utilitarian feel, while also being flirty and fun." With the chunkier style that harkens back to the '90s, you can add Mary Janes to your wardrobe without worrying about looking too sweet or too young.  

The chunky loafer

Another chunky '90s alternative to a classic style is the chunky loafer. While the classic flat loafer can look a little too corporate, the chunky loafer is a funkier style that adds a little drama to an iconic look. 

The look first skyrocketed to popularity in the '90s when every girl seemed to have a chunky loafer in her closet. Now, the statement look is back. As Glamour noted, designers like GANNI, Alexander McQueen, and Mango are all selling chunky loafers right now. And, at the 2022 London Fashion Week, everyone seemed to be wearing chunky loafers with oversized blazers and wide-leg trousers. 

According to You Magazine, the chunky loafer has slowly been coming back into style over the past few years, thanks to Prada. In fact, there was a reported 2000% increase in searches for loafers in 2020 alone. It sounds like this is one '90s trend that isn't going anywhere.

The white loafer

They always say never to wear white after Labor Day — unless, of course, you wear a white loafer. Loafers go in and out of fashion, but the white loafer is one look that always keeps coming back. White loafers are a great way to make a bold statement that still looks simple, timeless, and elegant.

White loafers exploded in the '90s, and they are still going strong today. In 2021, for instance, Katie Holmes was spotted sporting a pair of Gucci's Brixton loafers in white leather (via InStyle). Selena Gomez has also been spotted in the same pair of white Gucci loafers in 2018, which she paired with a maxi floral dress (via Vogue). What a summery '90s queen!

As one writer explained in The Guardian, white loafers make a great alternative to white sneakers in the summer. After all, they're fresh, light, and easy to slip on. Plus, they go with just about any outfit, whether you're dressing up for work or down for the weekend. 

The square toed heeled sandal

Few shoe looks scream the '90s more than the square-toed sandal with a large square heel. One look at these shoes, and you'll probably have flashbacks to Britney Spears or Paris Hilton. While these sandals may initially look a little dated, they are still very much on trend. 

According to Elite Daily, the sandals made a significant comeback in 2020, with Bottega Veneta's iconic pair causing quite the storm. Celebrities like Kylie Jenner, Kendall Jenner, and Hailey Bieber all jumped aboard the trend. 

These slip-on sandals are perfect for transitioning from day to night during the summer. Pair them with your favorite jeans and a baggy shirt in the day, or throw them on with a little black dress and a clutch bag in the evening for a going-out look. To really pay homage to the '90s version of the look, we recommend searching for a pair with a shorter one or two-inch heel that is wide and square at the bottom.

The platform sandal

One thing that the '90s knew how to do well was the platform shoe. Whether it was heels, flats, or sandals, there were platforms everywhere. The slip-on platform sandal was one look that epitomized the '90s. Think huge platform sole with an open-toed top. As Cosmopolitan noted, platform sandals are the perfect alternative to stilettos if you want to add some height without the pain of — you know — actual heels.

However, platform sandals may not be the best everyday look. As the New York Post reported in 2019, some doctors have warned against wearing slide-on platform sandals too often as they can be bad for the feet, ankles, and back in the long term. "You're not in proper alignment, so over time, that can add a lot of strain to your back," podiatrist Dr. Hillary Brenner said, adding that "nine times out of 10," ankle sprains come from this kind of shoe. Sounds like this is one throwback look to save for special occasions only.

The platform clog with studs

Yes, it's another platform shoe — we told you, the '90s were all about adding height to your shoes with towering platforms! This time, we're talking about the platform clog — with studs, of course. This bold shoe look may not be classically attractive, but it's certainly a look. Platform clogs first came to prominence in the '90s, and in 2021, they came back in full swing, with designers like Khaite, Isabel Marant, and Gucci all releasing updated platform clogs in their collections (via The Zoe Report).

To really nail the classic '90s look, aim for super high platforms — the chunkier, the better — and bold studs around the edge of the shoe. In other words, avoid subtlety at all costs. For instance, you could try these studded Chanel clogs with brown leather from 2010 or these Gucci Adidas clogs if you're keen to try the look for yourself.

The Converse All Star

A few shoe brands dominated the '90s, and Converse was one of the major players. These days, we all know about Converse shoes — in fact, the famous lace-up sneakers with the white rubber sole and the round star logo on the side are now instantly recognizable. The Converse All Star shoes were designed to be basketball shoes. They first took off in the '70s, but it was in the '90s when they became synonymous with the grunge movement. 

"The All Star becomes a part of culture in ways that Converse had never really originally intended... it goes on to have meaning in many different realms outside of basketball," Elizabeth Semmelhack, creative director and senior curator at the Bata Shoe Museum in Toronto, told Mr. Porter. "It's not about popping tags and having a crisp white pair — you wore what you had and you wore it to death."

Now, with the '90s fashion revival, these shoes are back in style. If you want to go for the classic grunge look, try pairing these sneakers with a pair of baggy jeans and a plain white tee. 

The classic Birkenstock sandal

There was a time when the Birkenstock was considered a serious fashion faux pas reserved only for out-of-touch dads and uncles. However, thanks to a resurgence in popularity of the ugly shoe in the fashion world, the infamous sandal with the cork sole and the double leather straps is officially back on trend. 

According to Vogue, the '90s trend of wearing Birkenstocks had become so popular by 2016 that fashion editors were even wearing them to work. And according to CNBC, sales of the famous Birkenstock sandal were going up, too. In 2019, for instance, sales rose by 140% at Nordstrom and 171% at Zappos in just three months. 

While the '90s saw some experimental Birkenstocks hitting the shelves, such as Narciso Rodriguez's cashmere Birkenstocks, these days, the classic Arizona sandals are all the rage. Whether you want to wear them with a sundress in the summer or you sport them with a pair of chunky socks and sweatpants in the winter, you can rest assured that Birkenstocks are still just as fashionable as ever. 

The heeled thong

Only a decade like the '90s could come up with a trend like the heeled thong. After all, mixing flip-flops and heels was a pretty ambitious move. However strange heeled thongs may seem to some, it turns out the '90s trend is still thriving. 

Back in the '90s, stars like Gwen Stefani and Britney Spears were often seen wearing heels with that iconic strap between the first and second toe, both out and about on the streets and at red carpet events. According to Refinery29, designers like Prada, Jill Sander, Burberry, and Bottega Veneta are behind the comeback of the heeled thong. 

While many heeled thongs in the '90s looked like flip flops with an awkward heel added, these days, some heeled thongs look a little more presentable. Take Jill Sander's streamlined thongs with the straight strap that reaches all the way down to the ankle or Karen Millen's elegant criss-cross design. It seems this look has been officially updated for the 21st century!

The Nike Air Max

While the '90s was undoubtedly a decade of platform shoes and heels, it was also a decade defined by the dad sneaker. On low-key days, everyone threw on a pair of chunky sneakers and mom jeans. And one of the go-to styles was the Nike Air Max 90. The Air Max featured a bouncy sole filled with air pockets and a simple block color design punctuated by the classic Nike tick. 

It seems that the Air Max sneakers are still going strong. The likes of Emily Ratajkowski, Rihanna, Rita Ora, and Zendaya have all been spotted in their Air Max sneakers in the past few years (via Lympo). 

If you're looking for the perfect throwback shoe for those lazy weekend days or those long-haul flights, Nike Air Max 90 is definitely the best way to go. Not only are these shoes undeniably comfortable, it's pretty clear that they're just as trendy as ever.

The cowboy boot

Thought cowboy boots were reserved for the ranch? Think again. Cowboy boots burst onto the scene in the '90s. Pamela Anderson famously sported a pair in 1993 with a pair of short shorts. Britney Spears was also a fan. Even Princess Diana got in on the trend (via The Times). 

Well, it seems that cowboy boots are still just as popular as they were three decades ago. As The Sun reported in 2018, cowboy boots appeared on the runways at various fashion weeks that year. Since then, celebrities have been wearing them everywhere. High-profile fans include the likes of Kendall Jenner, Emily Ratajkowski, Dua Lipa, and Jodie Comer (via Who What Wear and People).

The great thing about cowboy boots is their versatility. Pair them with a sundress and a big hat in the summer for a low-key, laid-back look. Or, wear them with a pair of structured trousers and a blazer for a chic, sophisticated going-out look. You can also experiment with different colors and styles. Try a pair of classic knee-high brown leather cowboy boots for an authentic Western look, or go for a sleek pair of mid-calf black leather boots to update the look for the city. With cowboy boots, anything goes!

The pointed toe knee-high boot

Knee-high heeled boots were all the rage in the '90s. You probably remember that episode of "Friends" when Monica bought a very expensive pair of boots and then proceeded to wear them even though they destroyed her feet (via YouTube). Naturally, those boots featured a pointed toe and a devastatingly high stiletto heel. As it turns out, this style is back in fashion. As Tiffany Hsu of MyTheresa told Who What Wear in 2022, "The midcalf and the knee-high boot is going to be bigger than ever, with designers focusing on this height and less on the ankle boot. The key trend from this was the boots worn under midi skirts, especially in bright ways."

As Gianna Nucci, a New York-based stylist, told Today in 2022, there are plenty of ways to wear knee-high heeled boots. "Maybe you have a lot of walking on your commute, so you would need a more durable style that's also comfortable," said Nucci. She warned there are "a lot of cute winter boots that aren't functional for rain and snow, so you want to be sure you're not just buying off aesthetic." Nucci suggested pairing your knee-high boots with leggings and a thick sweater or with skinny jeans and a jacket.

Doc Martens

Few shoe brands defined the '90s grunge trend quite like Doc Martens. In the '90s, the lace-up combat boot look exploded. When the '90s came back into fashion in the 2020s, Doc Martens again soared in popularity. According to The Guardian, the brand expanded in 2018, opening 16 new stores and enjoying a £50 million rise in profits. "This, in the context of the wider macroeconomic uncertainty that exists in a few of our key markets, is testament to both the strength of our brand, our heritage and consumer proposition and the execution of our strategy," said Paul Mason, the brand's chair.

Numerous celebrities have been seen wearing the famous grunge look, including Bella Hadid, Gigi Hadid, Cardi B, and Miley Cyrus. According to Who What Wear, the vegan alternative offers a softer, more comfortable option. Whichever type you choose, one thing's for sure — Doc Martens can be styled with pretty much any outfit. And by the looks of things, they never go out of style.

The clear mule

Cinderella who? Enter the clear mules, the '90s answer to the glass slipper. In the '90s, clear mules made of see-through plastic burst onto the scene. They popped up in nightclubs, on the streets, on our screens, and in pop concerts. 

While you may initially think these shoes look just a little tacky, they're actually incredibly easy to style as they go with everything. Plus, as Who What Wear pointed out, they add loads of length to your legs. With brands like Yeezy, Manolo Blahnik, and Alexander Wang all coming out with their own version of the '90s trend, it's safe to say that this look is definitely in. And, as Glamour noted, even Hollywood A-Lister Margot Robbie has hopped aboard this shoe trend, pairing her see-through heels with an all-white Gucci outfit. Kim Kardashian also has a pair of clear Yeezys, while Kirsten Dunst has a pair of strappy PVC Ferragamo sandals for red carpets. Consider us seriously inspired!